IL39719A - N-arylcarbamic acid esters,their preparation and their use as plant-growth regulators - Google Patents

N-arylcarbamic acid esters,their preparation and their use as plant-growth regulators

Info

Publication number
IL39719A
IL39719A IL7239719A IL3971972A IL39719A IL 39719 A IL39719 A IL 39719A IL 7239719 A IL7239719 A IL 7239719A IL 3971972 A IL3971972 A IL 3971972A IL 39719 A IL39719 A IL 39719A
Authority
IL
Israel
Prior art keywords
compound
carbon atoms
alkyl
process according
formula
Prior art date
Application number
IL7239719A
Other versions
IL39719A0 (en
Original Assignee
Bayer Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE2131028A external-priority patent/DE2131028B2/en
Priority claimed from DE19722214057 external-priority patent/DE2214057A1/en
Application filed by Bayer Ag filed Critical Bayer Ag
Publication of IL39719A0 publication Critical patent/IL39719A0/en
Publication of IL39719A publication Critical patent/IL39719A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Furan Compounds (AREA)

Claims (46)

1. N-arylcarbamic acid esters of the general formula .in which - - . - _. -- —- - R is alkyl,. alkynyl or haloalkyl, R1, R2 and R3, which may be identical or different, are each .' ^ hydrogen, alkyl, alkpxy:..or halogen, R. is alkyl, alkenyl, alkynyl, haloalkyl or optionally halo-'.' • gen substituted, phenyl, or is the grouping ■■' 1 R5-C- \ ·" ■ .· ■ " " '' ■ ' · · '· ' {' . wherein , ! R5 is hydrogen, alkyl, alkenyl, cycloalkyl, oycloalkenyl, halo- · '.' , alkyl, acylalkyl, alkoxycarbonylalky'l, an aryl radical optionally being substituted by alkyl, haloalkyl, alkoxy and/or halogen; an aralkyl or an aryloxyalkyl, the aryl part of the . two last-mentioned radicals optionally carrying one or more substituents selected from halogen, ' alkyl, haloalkyl or alkoxy, and the alkyl part of the aralkyl radical' optionally . being substituted by one or more halogen atoms; or R^ is 'the grouping - and Y and Υ· are oxygen or sulphur.
2. Compounds* according to Claim 1 in which R is straight- ' ' t chain or branched alkyl with 1 to 4 carbon efcoms, straight-chain or branched alkynyl with 3 to 6 carbon atoms or haloalkyl with 1 to.4 carbon atoms and 1 to 3 halogen atoms; R ,. R and ^ are each hydrogen, fluorine, chlorine, bromine, alkyl with 1 to carbon atoms or straight-chain or branbhed alkoxy with 1 to 4 carbon atoms; and R^ is straight-chain or branched alkyl with I tp' 6 carbon atoms or haloalkyl with 1 to 6 carbon atoms an 1 to 3 halogen atoms, straight-chain or branched alkenyl ' . •with 3 to 6 carbon atoms, straight-chain or branched alkynyl ;!■ with 3 to £ carbon atoms or phenyl optionally substituted 5 by one or more chlorine atoms, or is the grouping R -C=Y-' - wherein Y' is oxygen or sulphur and ^ is hydrogen, straight- chain or branched alkyl with 1 to 18 carbon atoms, straight- . chain or branched alkenyl, with 3 to 12 carbon atoms, cyclo- - alkyl with 3 to 8 carbon atoms,, cycloalkenyl with 5 to 8 carbon .atoms, haloalkyl with 1 to 6 carbon atoms and 1 to- 5 halogen atoms, acylalkyl with 1 to 4 carbon atoms in the acyl part and 1 to 4 carbon atoms in the alkyl part, alkoxycarbonyl- ... alkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to '· ·' 4 carbon atoms in the alkyl part, aryl with 6 to 10 carbon' atoms optionally being substituted by one or more radicals selected from halogen, straight-chain or branched alkyl or :· alkoxy with, in either case, 1 to 4 carbon atoms and haloalkyl with 1 or 2 carbon atoms and 1 to 5 halogen atoms, or an aralkyl or aryloxyalkyl radical with, in each case, ■6 to 10 carbon atoms in .the aryl moiety and A to 3. oarbon .· atoms in the alkyl moiety, the aryl part of. the two last-mentioned radicals optionally carrying one or more substituents * selected from fluorine', chlorine, bromine, straight-chain or branched alkyl or alkoxy with, in either case, 1 to 4 carbon : atoms and. haloalkyl with 1' or 2 carbon atoms and 1. to 5 halo- . gen atoms, and the alkyl part of the aralkyl radical optionally being substituted by one or more halogen atoms; or ^, is the grouping ..·*
3. « The compound of the formula )2
4. The compound of the formula )2
5. The compound of the formula
6. The compound of the formula
7. The compound of the formula
8. The compound of the formula
9. The compound of the formula
10. The compound of the formula
11. The compound of the formula
12. , The compound of the formula
13. The compound of the formula
14. · The compound of the formula
15. · The compounds hereinbefore mentioned in Tables 1 and 2.
16. The compounds hereinbefore mentioned in Tables 3 and 4·
17. A process for the preparation of an N-arylcarbamic acid ester according to any of claims 1 to 15 in which an N- chloromethyl-N^rylcarbamic acid ester of the general formula in which R, R^, R2 and R^ have the meanings stated in claim 1, is reacted (a) with a compound of the general formula H-Y-R4 (III) in which R and Y have the meanings stated in claim 1 , in the presence of an acid-hinding agent and optionally in the presence of a solvent or (b) with a compound of the general formula A-Y-R4 (IV) ·. in which R4 and Y have the meanings stated in claim 1 , and A represents a cation or a fraction of a cation, in the presence of a solvent.
18. A process according to claim 17(a) in which the reaction is effected in the presence of an inert organic solvent.
19. A process according to claim 17(a) or 18 in which the reaction is effected in the presence, as an acid-binding agent, of an alkali metal hydroxide, an alkali. metal carbonate or a tertiary organic base.
20. A process according to claim 19 in which the acid-binding agent is sodium carbonate, triethylamine or pyridine.
21. A process according to any of claims 17(a) and 18 to 20 in which the reaction is effected at from -20°C to +100°C.
22. A process according to claim 21 in which the reaction is effected at from - 10°0 to +80°C.
23. A process according to any of claims 17(a) and 18 to 22 in which 1 to 1.5 moles of the compound (III) and 1 to 2 moles of the acid-binding agent are used per mole of N-chloromethyl-N-arylcarbamic acid ester (II).
24. A process according to claims 17(b) in which A is an ammonium, alk lammonium, dialkylammonium ,trialkylammonium or alkali metal cation, or represents half of an alkaline earth metal cation.
25. A process according to claim 24 in which A is ammonium, dialkylammonium or trialkylammonium with 1 to 4 carbon atoms in each alkyl moiety, a sodium ion or a potassium ion, or represents half of a magnesium ion or of a calcium ion.
26. A process according to claim 17(b), 2 or 25 in which the reaction is effected in the presence of a polar organic solvent.
27. A process according to any of claims 17(b) and 24 to 26 in which the reaction is effected at from 0°C to 150°C.
28. A process according to claim 27 in which the reaction is effected at from 20°C to 100°C.
29. A process according to any of claims 17(b) and 2 to 28 in which the reactants (II) and (IV) are used in equimolar amounts.
30. A process according to any of claims: 17 to 29 in which the N-chloromethyl-N-arylcarbamic acid ester (II) is one that is hereinbefore specifically mentioned.
31. A process according to any of claims 17 to 30 in which the compound of the formula (III) or (IV) is one that is hereinbefore specifically mentioned.
32. A process for the preparation of a compound according to claim 1 substantially as hereinbefore described in any of Examples 1 to 4·
33. A process according to any of claims 17 to 29 adapted for the preparation of a compound according to claim 16.
34. Compounds, according to claim 1 whenever prepared by a process according to any of claims 17to 32.
35. Compounds according to claim 16 whenever prepared by a process according to any of claims 17 to 29.
36. A plant-growth-regulating caaposition containing as active ingredient a compound according to any of claims 1 to 15 and 34 in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.
37. A composition according to claim 36 containing from 0.1 to 95$ of the active compound, by weight.
38. A composition according to claim 37 containing from 0.5 to 90$ of the active compound, by weight.
39. A composition according to claim 36» 37 or 38 in which the active compound is according to claim 16 or 35.
40. A method of regulating the growth of plants which comprises, applying to the plants or a plant habitat a compound according to any of claims 1 to 15 and 34 alone or in the form of a composition containing as active ingredient a compound according to any of claims 1 to 15 and 34 in admixture with a diluent or carrier.
41. A method according to claim 40 in which the active compound is applied to an area of plant cultivatio in an amount of 0.1 to 25 kg per hectare.
42. A method according to claim 41 in which the active compound is applied to an area of plant cultivation in an amount of 0.5 to 20 kg per hectare.
43. A method according to claim 40, 41 or 42 in which the active compound is one that is hereinbefore mentioned in Example A or B.
44. A method according to claim 40, 41 or 42 in which the active compound is according to claim 16 or 35.
45. Plants of which the growth has been regulated by their being grown in areas in which immediately prior to and/or during the time of the growing a compound according to any of claims 1 to 15 and 34 was applied alone or in admixture with a diluent or carrier.
46. Plants according to claim 45 in which the active compound is according to claim 16 or 35»
IL7239719A 1971-06-23 1972-06-20 N-arylcarbamic acid esters,their preparation and their use as plant-growth regulators IL39719A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2131028A DE2131028B2 (en) 1971-06-23 1971-06-23 N-Aryl carbamic acid esters, process for their preparation and their use as plant growth regulators
DE19722214057 DE2214057A1 (en) 1972-03-23 1972-03-23 Substd n-aryl n-methyl carbamic acid esters - plant growth regulators

Publications (2)

Publication Number Publication Date
IL39719A0 IL39719A0 (en) 1972-08-30
IL39719A true IL39719A (en) 1976-01-30

Family

ID=25761312

Family Applications (1)

Application Number Title Priority Date Filing Date
IL7239719A IL39719A (en) 1971-06-23 1972-06-20 N-arylcarbamic acid esters,their preparation and their use as plant-growth regulators

Country Status (16)

Country Link
US (1) US3920727A (en)
JP (1) JPS563342B1 (en)
AT (1) AT317609B (en)
BE (1) BE785264A (en)
CA (1) CA1025458A (en)
CH (1) CH584504A5 (en)
DD (2) DD107910A5 (en)
DK (1) DK131854C (en)
EG (1) EG10699A (en)
FR (1) FR2144302A5 (en)
GB (1) GB1339116A (en)
HU (1) HU165294B (en)
IL (1) IL39719A (en)
IT (1) IT960711B (en)
NL (1) NL7208585A (en)
SE (1) SE380519B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4230874A (en) * 1976-09-13 1980-10-28 Stauffer Chemical Company N-(Benzenesulfonyl) carbamates-herbicidal antidotes
US4293701A (en) * 1976-09-13 1981-10-06 Stauffer Chemical Company N-(Benzenesulfonyl) carbamates - herbicidal antidotes
DE2730325A1 (en) * 1977-07-01 1979-01-11 Schering Ag CARBANILIC ACID-(3-UREIDO-PHENYL)- ESTER, PROCESS FOR THE PREPARATION OF THESE COMPOUNDS, AND HERBICIDES CONTAINING THEM
DE2732848A1 (en) * 1977-07-18 1979-02-08 Schering Ag DIURETHANE, HERBICIDAL AGENTS CONTAINING THESE COMPOUNDS AND THE PROCESS FOR THEIR PRODUCTION
US4419523A (en) * 1979-12-31 1983-12-06 Stauffer Chemical Company N-(Benzenesulfonyl) carbamates-herbicidal antidotes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3547977A (en) * 1967-10-27 1970-12-15 Velsicol Chemical Corp Novel carbanilates

Also Published As

Publication number Publication date
DK131854B (en) 1975-09-15
DK131854C (en) 1976-02-16
US3920727A (en) 1975-11-18
DD100621A5 (en) 1973-10-05
CH584504A5 (en) 1977-02-15
NL7208585A (en) 1972-12-28
BE785264A (en) 1972-12-22
FR2144302A5 (en) 1973-02-09
IL39719A0 (en) 1972-08-30
SE380519B (en) 1975-11-10
AT317609B (en) 1974-09-10
GB1339116A (en) 1973-11-28
DD107910A5 (en) 1974-08-20
JPS563342B1 (en) 1981-01-24
HU165294B (en) 1974-08-28
CA1025458A (en) 1978-01-31
EG10699A (en) 1976-07-31
IT960711B (en) 1973-11-30

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